After four defeats on the trot, it was imperative for the Blues to stop the rot, but yet another late strike saw the Spireites slump to a fifth consecutive loss.
Martin Allen made two changes to the team that lost to Hartlepool United. Hadyn Hollis and Sam Muggleton were dropped to the bench in favour for Laurence Maguire and the returning Jerome Binnom-Williams.
Even after five defeats, the hosts started brightly and created the first chance through Gozie Ugwu. However, the striker's shot was straight at Dean Brill.
Binnom-Williams continued the pressure as the home side's main threat. His pace and strength was enough to get the winger into the box before his cut-back was cleared by the Orient defence.
Brill was called into action once more on the 10th minute when he made a fantastic save after Zavon Hines connected to Drew Talbot's cross.
The visitors weren't just about to let Chesterfield have all the chances, though. Callum Burton was called upon to tip Josh Coulson's header over the crossbar.
Binnom-Williams continued to have the Leyton Orient back line on the ropes as he linked up well with Ugwu before he scuffed his shot slightly wide of the goal.
Five minutes later, those two almost combined to open the scoring. This time Binnom-Williams turned provider as his cross was inches away from Ugwu opening his account for Chesterfield.
Orient would have to wait until the second half to test the Spireites goalkeeper. However, Burton reacted well after Marvin Ekpiteta couldn't fully connect from the free kick.
The home side then came inches away from opening the scoring. Binnom-Williams fiercely struck free kick had Brill beaten but the ball cannoned off the post.
On the 62nd minute, the O's were given a golden chance to take the lead. Macauley Bonne was left unmarked by Will Evans. The striker, who scored 22 National League goals last season, somehow headed wide of the Chesterfield goal.
Luckily for Bonne, James Dayton made no mistake with 12 minutes to go. The Blues failed to clear their lines which allowed the midfielder space to fire into the top left hand corner of the goal.
The Spireites were unable to push for the equaliser and fell to a fifth consecutive defeat in the National League.
Post-Match Verdict: Mistakes cost the Spireites once again
If there has been anything missing in the previous couple of games, it's been a good performance. However, in the first half, Chesterfield were looking dangerous going forward and solid at the back.
The only problem is that one mistake is costing the Spireites once more. The defence gave Dayton too much space and there was nothing Burton could do about the goal.
Jerome Binnom-Williams provided the Blues with pace and strength down the wings and was my man of the match.
If Martin Allen can get his team playing like they did in the first half for the whole 90 minutes, then results will soon go Chesterfield's way.
I still don't think it will hurt to get another midfielder and possibly another striker in on loan. However, the players will take some positives from the game against Orient and hopefully find themselves with six points come 5pm next Saturday.